Compound characterization data — Sharad Singh et al., 2026

Sharad Singh, Chandresh Jagani, Gauri Gawas, Rohitkumar Gajera, Nirav Dhabhi, Viransinh Mahida, Paranjay Parikh, Vinod Sanna, Gajendrasinh Raolji, Sasikumar Kuttappan. “Structural diversification of PRE-084-derived 2-morpholinoethyl-1-arylcyclohexane-1-carboxylates reveals distinct mitochondrial membrane potential phenotypes.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007609/v1

No separate supporting information file was found among the files available from the ChemRxiv record

1-(4-chlorophenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, CDCl₃)	δ 7.47 (d, J = 8.8 Hz, 2H), 7.40 (d, J = 8.8 Hz, 2H), 2.17 (d, J = 12.4 Hz, 2H), 1.90–1.73 (m, 7H), 1.37–1.25 (m, 2H)

1-(4-chlorophenyl)cyclohexane-1-carboxylic acid
¹H NMR (400 MHz, DMSO-d₆)	δ 12.47 (s, 1H), 7.41 (s, 4H), 2.30 (d, J = 12.8 Hz, 2H), 1.64–1.51 (m, 5H), 1.45–1.37 (m, 2H), 1.26–1.22 (m, 1H)

2-Morpholinoethyl 1-(4-chlorophenyl)cyclohexane-1-carboxylate
Identifier	PIR-086; 6b
¹H NMR (400 MHz, DMSO-d₆)	δ 7.41 (s, 4H), 4.16 (t, J = 5.2 Hz, 2H), 3.47 (t, J = 4.4 Hz, 4H), 2.44 (t, J = 5.2 Hz, 2H), 2.37 (d, J = 13.2 Hz, 2H), 2.29–2.27 (m, 4H), 1.69–1.57 (m, 5H), 1.51–1.43 (m, 2H), 1.30–1.22 (m, 1H)
MS (ESI)	m/z 352.73 [M+H]⁺

2-Morpholinoethyl 1-phenylcyclohexane-1-carboxylate
Identifier	PIR-084; 6a
¹H NMR (400 MHz, DMSO-d₆)	δ 7.31–7.30 (m, 4H), 7.22 (d, J = 6.8 Hz, 1H), 4.13 (t, J = 5.2 Hz, 2H), 3.46 (t, J = 4.0 Hz, 4H), 2.46–2.43 (m, 2H), 2.39–2.35 (m, 2H), 2.37 (br s, 4H), 1.66–1.41 (m, 5H), 1.50–1.41 (m, 2H), 1.27–1.16 (m, 1H)
MS (ESI)	m/z 318.4 [M+H]⁺

1-(4-bromophenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, DMSO-d₆)	δ 7.53 (d, J = 8.8 Hz, 2H), 7.38 (d, J = 8.4 Hz, 2H), 2.15 (d, J = 12.4 Hz, 2H), 1.89–1.70 (m, 7H), 1.30–1.27 (m, 2H)

1-(4-bromophenyl)cyclohexane-1-carboxylic acid
MS (ESI)	m/z 283.0 [M+H]⁺

2-Morpholinoethyl 1-(4-bromophenyl)cyclohexane-1-carboxylate
Identifier	PIR-102; 6c
¹H NMR (400 MHz, DMSO-d₆)	δ 7.53 (d, J = 8.8 Hz, 2H), 7.33 (d, J = 8.8 Hz, 2H), 4.15 (t, J = 5.2 Hz, 2H), 3.47 (t, J = 4.4 Hz, 4H), 2.49–2.43 (m, 2H), 2.36–2.33 (m, 2H), 2.28–2.26 (m, 4H), 1.68–1.56 (m, 5H), 1.51–1.44 (m, 2H), 1.34–1.18 (m, 1H)
MS (ESI)	m/z 396.0 [M+H]⁺

1-(4-methoxyphenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, CDCl₃)	δ 7.42 (d, J = 8.8 Hz, 2H), 6.93 (d, J = 8.8 Hz, 2H), 3.83 (s, 3H), 2.16 (d, J = 12.4 Hz, 2H), 1.87–1.76 (m, 5H), 1.74–1.70 (m, 2H), 1.30–1.24 (m, 2H), 0.90–0.86 (m, 1H)

1-(4-methoxyphenyl)cyclohexane-1-carboxylic acid
¹H NMR (400 MHz, DMSO-d₆)	δ 12.23 (s, 1H), 7.29 (d, J = 6.8 Hz, 2H), 6.89 (d, J = 6.8 Hz, 2H), 3.73 (s, 3H), 2.30 (d, J = 12.0 Hz, 2H), 1.61–1.56 (m, 5H), 1.45–1.35 (m, 2H), 1.26–1.21 (m, 1H)

2-Morpholinoethyl 1-(4-methoxyphenyl)cyclohexane-1-carboxylate
Identifier	PIR-098; 6d
¹H NMR (400 MHz, DMSO-d₆)	δ 7.27 (d, J = 6.8 Hz, 2H), 6.87 (d, J = 9.2 Hz, 2H), 4.11 (t, J = 5.2 Hz, 2H), 3.72 (s, 3H), 3.47 (t, J = 4.4 Hz, 4H), 2.44 (t, J = 5.2 Hz, 2H), 2.37–2.34 (m, 2H), 2.27 (br s, 4H), 1.63–1.59 (m, 5H), 1.48–1.42 (m, 2H), 1.24–1.21 (m, 1H)
MS (ESI)	m/z 348.2 [M+H]⁺

1-(4-(trifluoromethyl)phenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, DMSO-d₆)	δ 7.56–7.52 (m, 4H), 2.10 (d, J = 12.8 Hz, 2H), 1.85–1.70 (m, 6H), 1.63–1.53 (m, 2H)

1-(4-(trifluoromethyl)phenyl)cyclohexane-1-carboxylic acid
¹H NMR (400 MHz, DMSO-d₆)	δ 7.85 (br s, 4H), 2.43–2.30 (m, 2H), 1.52–1.48 (m, 8H)

2-Morpholinoethyl 1-(4-(trifluoromethyl)phenyl)cyclohexane-1-carboxylate
Identifier	PIR-100; 6e
¹H NMR (400 MHz, DMSO-d₆)	δ 7.72 (d, J = 8.4 Hz, 2H), 7.62 (d, J = 8.4 Hz, 2H), 4.17 (t, J = 5.2 Hz, 2H), 3.45 (t, J = 4.4 Hz, 4H), 2.48–2.34 (m, 4H), 2.26 (br s, 4H), 1.72–1.48 (m, 5H), 1.51–1.48 (m, 2H), 1.27–1.25 (m, 1H)
MS (ESI)	m/z 386.0 [M+H]⁺

1-(3-methoxyphenyl)cyclohexane-1-carboxylic acid
¹H NMR (400 MHz, DMSO-d₆)	δ 12.47 (s, 1H), 7.24 (dt, J = 11.8, 8.0 Hz, 1H), 7.01–6.80 (m, 3H), 3.74 (s, 3H), 2.33 (d, J = 13.6 Hz, 2H), 1.58 (q, J = 15.7 Hz, 5H), 1.48–1.37 (m, 2H), 1.23 (d, J = 10.2 Hz, 1H)

2-Morpholinoethyl 1-(3-methoxyphenyl)cyclohexane-1-carboxylate
Identifier	PIR-099; 6f
¹H NMR (400 MHz, DMSO-d₆)	δ 7.27 (t, J = 8.0 Hz, 1H), 6.95 (dd, J = 8.1, 1.9 Hz, 1H), 6.91–6.81 (m, 2H), 4.16 (t, J = 5.5 Hz, 2H), 3.75 (s, 3H), 3.49 (t, J = 4.6 Hz, 4H), 2.48 (t, J = 5.5 Hz, 2H), 2.38 (d, J = 12.5 Hz, 2H), 2.30 (t, J = 4.7 Hz, 4H), 1.64 (m, 5H), 1.48 (t, J = 12.7 Hz, 2H), 1.20 (d, J = 6.3 Hz, 1H)
MS (ESI)	m/z 348.42 [M+H]⁺

1-(3-(trifluoromethyl)phenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, CDCl₃)	δ 7.58–7.53 (m, 4H), 1.89–1.75 (m, 5H), 1.59 (br s, 2H), 1.37–1.27 (m, 2H), 1.24–1.22 (m, 1H)

1-(3-(trifluoromethyl)phenyl)cyclohexane-1-carboxylic acid
¹H NMR (400 MHz, DMSO-d₆)	δ 7.73–7.68 (m, 1H), 7.66–7.57 (m, 3H), 2.33 (d, J = 12.8 Hz, 2H), 1.71–1.54 (m, 5H), 1.48–1.41 (m, 2H), 1.29–1.24 (m, 1H)

2-Morpholinoethyl 1-(3-(trifluoromethyl)phenyl)cyclohexane-1-carboxylate
Identifier	PIR-101; 6g
¹H NMR (400 MHz, DMSO-d₆)	δ 7.70 (d, J = 7.6 Hz, 1H), 7.65–7.57 (m, 3H), 4.16 (t, J = 5.2 Hz, 2H), 3.44–3.42 (m, 4H), 2.45–2.38 (m, 4H), 2.23 (br s, 4H), 1.73–1.56 (m, 5H), 1.52–1.44 (m, 2H), 1.28–1.17 (m, 1H)
MS (ESI)	m/z 386.4 [M+H]⁺

1-(3-phenoxyphenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, CDCl₃)	δ 7.36 (q, J = 7.2, 14.4 Hz, 3H), 7.18–7.13 (m, 2H), 7.03 (d, J = 8.0 Hz, 2H), 6.93 (d, J = 8.0 Hz, 1H), 2.18 (d, J = 12.4 Hz, 2H), 1.87–1.71 (m, 6H), 1.30–1.27 (m, 2H)

2-Morpholinoethyl 1-(3-phenoxyphenyl)cyclohexane-1-carboxylate
Identifier	PIR-105; 6h
¹H NMR (400 MHz, DMSO-d₆)	δ 7.42–7.33 (m, 3H), 7.17–7.13 (m, 2H), 7.01–6.98 (m, 3H), 6.87 (dd, J = 1.6, 7.6 Hz, 1H), 4.14 (t, J = 5.6 Hz, 2H), 3.47 (t, J = 4.4 Hz, 4H), 2.44 (t, J = 5.6 Hz, 2H), 2.34–2.28 (m, 6H), 1.65–1.55 (m, 5H), 1.48–1.39 (m, 2H), 1.28–1.19 (m, 1H)
MS (ESI)	m/z 410.2 [M+H]⁺

1-(3,4-dichlorophenyl)cyclohexane-1-carbonitrile
MS (ESI)	m/z 352.2 [M−H]⁻

2-Morpholinoethyl 1-(3,4-dichlorophenyl)cyclohexane-1-carboxylate
Identifier	PIR-088; 6i
¹H NMR (400 MHz, DMSO-d₆)	δ 7.61 (d, J = 8.8 Hz, 1H), 7.55 (d, J = 2.4 Hz, 1H), 7.37 (dd, J = 2.4, 8.4 Hz, 1H), 4.16 (t, J = 5.2 Hz, 2H), 3.45 (t, J = 4.4 Hz, 4H), 2.45 (t, J = 5.2 Hz, 2H), 2.34 (d, J = 12.4 Hz, 2H), 2.27–2.25 (m, 4H), 1.71–1.47 (m, 7H), 1.34–1.24 (m, 1H)
MS (ESI)	m/z 386.0 [M+H]⁺

4-(bromomethyl)-1-chloro-2-(trifluoromethyl)benzene
MS (ESI)	m/z 272.8 [M+H]⁺

2-(4-chloro-3-(trifluoromethyl)phenyl)acetonitrile
¹H NMR (400 MHz, DMSO-d₆)	δ 7.88 (s, 1H), 7.80 (d, J = 8.4 Hz, 1H), 7.72 (d, J = 8.4 Hz, 1H), 4.19 (s, 2H)

1-(4-chloro-3-(trifluoromethyl)phenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, DMSO-d₆)	δ 7.92–7.88 (m, 2H), 7.82 (d, J = 8.4 Hz, 1H), 2.09 (d, J = 13.2 Hz, 2H), 1.94–1.82 (m, 4H), 1.75–1.72 (m, 1H), 1.67–1.59 (m, 2H), 1.57–1.37 (m, 1H)

1-(4-chloro-3-(trifluoromethyl)phenyl)cyclohexane-1-carboxylic acid
MS (ESI)	m/z 304.85 [M−H]⁻

2-Morpholinoethyl 1-(4-chloro-3-(trifluoromethyl)phenyl)cyclohexane-1-carboxylate
Identifier	PIR-129; 6j
¹H NMR (400 MHz, DMSO-d₆)	δ 7.71 (s, 3H), 4.17 (t, J = 5.6 Hz, 2H), 3.43 (t, J = 4.4 Hz, 4H), 2.45–2.37 (m, 4H), 2.25–2.23 (m, 4H), 1.75–1.69 (m, 2H), 1.63–1.56 (m, 3H), 1.52–1.46 (m, 2H), 1.49–1.28 (m, 1H)
MS (ESI)	m/z 420.07 [M+H]⁺

4-(bromomethyl)-1-chloro-2-methoxybenzene
¹H NMR (400 MHz, CDCl₃)	δ 7.38 (d, J = 11.2 Hz, 1H), 7.00–6.90 (m, 2H), 4.50 (s, 2H), 3.96 (s, 3H)

2-(4-chloro-3-methoxyphenyl)acetonitrile
¹H NMR (400 MHz, DMSO-d₆)	δ 7.46 (d, J = 8.4 Hz, 1H), 7.15 (d, J = 1.6 Hz, 1H), 6.69 (dd, J = 8.0, 2.0 Hz, 1H), 4.05 (s, 2H), 3.34 (s, 3H)

1-(4-chloro-3-methoxyphenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, DMSO-d₆)	δ 7.49 (d, J = 8.0 Hz, 1H), 7.23 (d, J = 2.4 Hz, 1H), 7.14 (dd, J = 8.0, 2.0 Hz, 1H), 3.90 (s, 3H), 2.10 (d, J = 12.8 Hz, 2H), 1.89–1.73 (m, 4H), 1.68–1.65 (m, 2H), 1.65–1.58 (m, 2H), 1.28–1.25 (m, 1H)

1-(4-chloro-3-methoxyphenyl)cyclohexane-1-carboxylic acid
MS (ESI)	m/z 266.9 [M−H]⁻

2-Morpholinoethyl 1-(4-chloro-3-methoxyphenyl)cyclohexane-1-carboxylate
Identifier	PIR-131; 6k
¹H NMR (400 MHz, DMSO-d₆)	δ 7.38 (d, J = 8.4 Hz, 1H), 7.03 (d, J = 1.6 Hz, 1H), 6.95 (dd, J = 8.0, 2.0 Hz, 1H), 4.18 (t, J = 5.6 Hz, 2H), 3.87 (s, 3H), 3.47 (t, J = 4.4 Hz, 4H), 2.47 (t, J = 5.6 Hz, 2H), 2.47–2.38 (m, 2H), 2.28 (br s, 4H), 1.70–1.58 (m, 5H), 1.52–1.43 (m, 2H), 1.28–1.25 (m, 1H)
MS (ESI)	m/z 382.4 [M+H]⁺

1-(3,4,5-trifluorophenyl)cyclohexane-1-carbonitrile
¹H NMR (400 MHz, CDCl₃)	δ 7.56–7.52 (m, 2H), 2.09 (d, J = 12.8 Hz, 2H), 1.85–1.70 (m, 5H), 1.63–1.53 (m, 2H), 1.32–1.22 (m, 1H)

2-Morpholinoethyl 1-(3,4,5-trifluorophenyl)cyclohexane-1-carboxylate
Identifier	PIR-103; 6l
¹H NMR (400 MHz, MeOD)	δ 7.23–7.19 (m, 2H), 4.26 (t, J = 5.2 Hz, 2H), 3.63 (t, J = 4.4 Hz, 4H), 2.60 (t, J = 5.6 Hz, 2H), 2.47–2.43 (m, 6H), 1.73–1.67 (m, 5H), 1.57–1.42 (m, 2H), 1.33–1.30 (m, 1H)
MS (ESI)	m/z 372.0 [M+H]⁺

Ethyl 1-(pyrimidin-2-yl)cyclohexane-1-carboxylate
MS (ESI)	m/z 235.2 [M+H]⁺

1-(pyrimidin-2-yl)cyclohexane-1-carboxylic acid
MS (ESI)	m/z 207.2 [M+H]⁺

2-Morpholinoethyl 1-(pyrimidin-2-yl)cyclohexane-1-carboxylate
Identifier	PIR-089; 6m
¹H NMR (400 MHz, DMSO-d₆)	δ 8.74 (d, J = 8.8 Hz, 2H), 7.20 (t, J = 4.8 Hz, 1H), 4.38 (t, J = 5.4 Hz, 2H), 3.73 (t, J = 4.8 Hz, 4H), 2.73 (t, J = 5.6 Hz, 2H), 2.55–2.54 (m, 4H), 2.37–2.33 (m, 2H), 2.19–2.13 (m, 2H), 1.67–1.55 (m, 5H), 1.46–1.44 (m, 1H)
MS (ESI)	m/z 320.2 [M+H]⁺

Diethyl 2-(5-chloropyrimidin-2-yl)malonate
MS (ESI)	m/z 273.0 [M+H]⁺

Ethyl 2-(5-chloropyrimidin-2-yl)acetate
MS (ESI)	m/z 201 [M+H]⁺

Ethyl 1-(5-chloropyrimidin-2-yl)cyclohexane-1-carboxylate
¹H NMR (400 MHz, CDCl₃)	δ 8.66 (s, 2H), 4.20 (q, J = 7.2 Hz, 2H), 2.32–2.28 (m, 2H), 2.14–2.09 (m, 2H), 1.61–1.52 (m, 5H), 1.41–1.39 (m, 1H), 1.22 (t, J = 7.2 Hz, 3H)

1-(5-chloropyrimidin-2-yl)cyclohexane-1-carboxylic acid
MS (ESI)	m/z 241.23 [M+H]⁺

2-Morpholinoethyl 1-(5-chloropyrimidin-2-yl)cyclohexane-1-carboxylate
Identifier	PIR-090; 6n
¹H NMR (400 MHz, DMSO-d₆)	δ 8.94 (s, 2H), 4.14 (t, J = 5.2 Hz, 2H), 4.48 (t, J = 4.8 Hz, 4H), 2.52 (t, J = 1.6 Hz, 2H), 2.26 (br s, 4H), 2.15–2.05 (m, 4H), 1.52 (br s, 5H), 1.39–1.35 (m, 1H)
MS (ESI)	m/z 354.0 [M+H]⁺