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170985-85-0

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Basic Information
CAS No.: 170985-85-0
Name: 2-[(1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl]hydrazinecarboxaldehyde
Article Data: 7
Molecular Structure:
Molecular Structure of 170985-85-0 (2-[(1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl]hydrazinecarboxaldehyde)
Formula: C13H20N2O2
Molecular Weight: 236.314
Synonyms: Hydrazinecarboxaldehyde,2-[1-ethyl-2-(phenylmethoxy)propyl]-, [S-(R*,R*)]-;N'-[(2S,3S)-2-(benzyloxy)pentan-3-yl]formic hydrazide;
EINECS: 1308068-626-2
Density: 1.042 g/cm3
Boiling Point: 338.531 °C at 760 mmHg
Flash Point: 158.538 °C
PSA: 50.36000
LogP: 3.03860
Related products
Synthetic route
74-96-4

ethyl bromide

170985-84-9

(S)-N'-(2-(benzyloxy)propylidene) formohydrazide

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Stage #1: ethyl bromide With iodine; magnesium In tert-butyl methyl ether at 40 - 55℃; for 2h; Inert atmosphere;
Stage #2: (S)-N'-(2-(benzyloxy)propylidene)formylhydrazide With N,O-bis-(trimethylsilyl)-acetamide In tert-butyl methyl ether at 5 - 30℃; for 9h; Temperature; Inert atmosphere;		66%
Stage #1: ethyl bromide With iodine; magnesium In tert-butyl methyl ether at 40 - 53℃; for 2h; Inert atmosphere;
Stage #2: (S)-N'-(2-(benzyloxy)propylidene)formylhydrazide With N,O-bis-(trimethylsilyl)-acetamide In tert-butyl methyl ether at 5 - 30℃; for 9h; Temperature; Inert atmosphere;		60%
Stage #1: ethyl bromide With iodine; magnesium In tert-butyl methyl ether at 40 - 55℃; for 2h; Inert atmosphere;
Stage #2: (S)-N'-(2-(benzyloxy)propylidene)formylhydrazide With N,O-bis-(trimethylsilyl)-acetamide In tert-butyl methyl ether at 0 - 30℃; Inert atmosphere;		48 g
Stage #1: ethyl bromide With iodine; magnesium In tert-butyl methyl ether at 40 - 55℃; Inert atmosphere;
Stage #2: (S)-N'-(2-(benzyloxy)propylidene)formylhydrazide With N,O-bis-(trimethylsilyl)-acetamide In tert-butyl methyl ether at 25 - 30℃; for 1.75h; Inert atmosphere;
925-90-6

ethylmagnesium bromide

(S)-2-(Benzyloxy)-N-(Formylamino)-Propanimine

A

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

B

N'-((2S,3R)-2-(benzyloxy)pent-3-yl)formylhydrazine

Conditions
ConditionsYield
Stage #1: (S)-2-(Benzyloxy)-N-(Formylamino)-Propanimine With N,N-bis(trimethylsilyl)acetamide In diethyl ether at 20℃; for 0.75h;
Stage #2: ethylmagnesium bromide In diethyl ether at 20℃; Grignard addition;		A 62.3%
B n/a
...Expand
81445-44-5

(S)-2-(benzyloxy)propanal

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 80 percent / methanol
2.1: bis(trimethylsilyl) acetamide / diethyl ether / 0.75 h / 20 °C
2.2: 62.3 percent / diethyl ether / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: toluene; methanol / 4 h / 0 - 30 °C
2.1: magnesium; iodine / tert-butyl methyl ether / 2 h / 40 - 55 °C / Inert atmosphere
2.2: 0 - 30 °C / Inert atmosphere
View Scheme
122151-32-0

(S)-2-(benzyloxy)-1-(pyrrolidin-1-yl)propan-1-one

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 94 percent / Red-Al / toluene / 5 h
2.1: 80 percent / methanol
3.1: bis(trimethylsilyl) acetamide / diethyl ether / 0.75 h / 20 °C
3.2: 62.3 percent / diethyl ether / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: magnesium / tetrahydrofuran / 1 h / 60 - 65 °C / Inert atmosphere; Large scale
1.2: 1 h / 0 - 5 °C / Inert atmosphere; Large scale
2.1: sodium tetrahydroborate; lithium bromide; zinc dibromide / tetrahydrofuran / 0 - 5 °C / Inert atmosphere; Large scale
3.1: dmap / dichloromethane / 0.17 h / 0 - 20 °C / Large scale
3.2: 13 h / 30 - 35 °C / Large scale
4.1: hydrazine hydrate / ethanol / 13 h / 25 - 70 °C / Large scale
4.2: 1 h / 20 °C / Large scale
5.1: methanol / 4 h / 50 - 55 °C / Large scale
View Scheme
77287-11-7

methyl (S)-2-(benzyloxy)propanoate

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diisobutylaluminium hydride / toluene / 3 h / -75 - -70 °C / Inert atmosphere
1.2: Inert atmosphere
2.1: toluene; methanol / 4 h / 0 - 30 °C
3.1: magnesium; iodine / tert-butyl methyl ether / 2 h / 40 - 55 °C / Inert atmosphere
3.2: 0 - 30 °C / Inert atmosphere
View Scheme

(S)-1-phenylethanamine (S)-2-(benzyloxy)propanoic acid

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 0 - 10 °C
2.1: diisobutylaluminium hydride / toluene / 3 h / -75 - -70 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: toluene; methanol / 4 h / 0 - 30 °C
4.1: magnesium; iodine / tert-butyl methyl ether / 2 h / 40 - 55 °C / Inert atmosphere
4.2: 0 - 30 °C / Inert atmosphere
View Scheme
53346-03-5

2-benzyloxypropionic acid methyl ester

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: water; sodium hydroxide / 5 h / 0 - 30 °C
2.1: toluene / 6 h / 25 - 30 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 0 - 10 °C
4.1: diisobutylaluminium hydride / toluene / 3 h / -75 - -70 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: toluene; methanol / 4 h / 0 - 30 °C
6.1: magnesium; iodine / tert-butyl methyl ether / 2 h / 40 - 55 °C / Inert atmosphere
6.2: 0 - 30 °C / Inert atmosphere
View Scheme
100-44-7

benzyl chloride

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium tert-butylate / N,N-dimethyl-formamide / 5 h / -20 - -10 °C
2.1: water; sodium hydroxide / 5 h / 0 - 30 °C
3.1: toluene / 6 h / 25 - 30 °C
4.1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 0 - 10 °C
5.1: diisobutylaluminium hydride / toluene / 3 h / -75 - -70 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: toluene; methanol / 4 h / 0 - 30 °C
7.1: magnesium; iodine / tert-butyl methyl ether / 2 h / 40 - 55 °C / Inert atmosphere
7.2: 0 - 30 °C / Inert atmosphere
View Scheme
33106-32-0, 74431-49-5, 100836-85-9, 6625-78-1

2-(benzyloxy)propanoic acid

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: toluene / 6 h / 25 - 30 °C
2.1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 0 - 10 °C
3.1: diisobutylaluminium hydride / toluene / 3 h / -75 - -70 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: toluene; methanol / 4 h / 0 - 30 °C
5.1: magnesium; iodine / tert-butyl methyl ether / 2 h / 40 - 55 °C / Inert atmosphere
5.2: 0 - 30 °C / Inert atmosphere
View Scheme

2-[2S-1-ethyl-2-benzyloxypropylidene]hydrazinecarbaldehyde

170985-85-0

N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide

Conditions
ConditionsYield
With sodium tetrahydroborate In isopropyl alcohol at 0 - 15℃; for 3h;9.1 g
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  • 2-[(1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl]hydrazinecarboxaldehyde

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  • N'-((2S,3S)-2-(Benzyloxy)pentan-3-yl)formohydrazide

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Specification

The 2-[(1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl]hydrazinecarboxaldehyde, with the CAS registry number 170985-85-0, has the systematic name of N'-[(2S,3S)-2-(benzyloxy)pentan-3-yl]formic hydrazide. And the molecular formula of the chemical is C13H20N2O2.

The characteristics of this chemical are as followings: (1)ACD/LogP: 2.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3; (4)ACD/LogD (pH 7.4): 3; (5)ACD/BCF (pH 5.5): 55; (6)ACD/BCF (pH 7.4): 55; (7)ACD/KOC (pH 5.5): 613; (8)ACD/KOC (pH 7.4): 614; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 50.36 Å2; (13)Index of Refraction: 1.511; (14)Molar Refractivity: 68.006 cm3; (15)Molar Volume: 226.851 cm3; (16)Polarizability: 26.96×10-24cm3; (17)Surface Tension: 37.676 dyne/cm; (18)Density: 1.042 g/cm3; (19)Flash Point: 158.538 °C; (20)Enthalpy of Vaporization: 58.189 kJ/mol; (21)Boiling Point: 338.531 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=CNN[C@H]([C@@H](OCc1ccccc1)C)CC
(2)InChI: InChI=1/C13H20N2O2/c1-3-13(15-14-10-16)11(2)17-9-12-7-5-4-6-8-12/h4-8,10-11,13,15H,3,9H2,1-2H3,(H,14,16)/t11-,13-/m0/s1
(3)InChIKey: LNEGZKZTVLXZFX-AAEUAGOBBS