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tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

Product Name
tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate
CAS No.
107017-73-2
Chemical Name
tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate
Synonyms
tert-Butyl [1-(Hydroxymethyl)cyclopropyl]carbamate;tert-butyl N-[1-(hydroxymethyl)cyclopropyl]carbamate;SKL325;Boc-ACPC-ol;Boc-1-Amnocyclopropylmethanol;Boc-1-Aminocyclopropylmethanol;1-(Boc-amino)cyclopropylmethanol;Boc-1-aminocyclopropane methanol;N-Boc-1-AMinocyclopropylMethanol;1-Boc-Amino-cyclopropanemethanol
CBNumber
CB91508201
Molecular Formula
C9H17NO3
Formula Weight
187.24
MOL File
107017-73-2.mol
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tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate Property

Melting point:
81.0 to 85.0 °C
Boiling point:
294.5±9.0 °C(Predicted)
Density 
1.11±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
form 
powder to crystal
pka
12.24±0.20(Predicted)
color 
White to Orange to Green
InChI
InChI=1S/C9H17NO3/c1-8(2,3)13-7(12)10-9(6-11)4-5-9/h11H,4-6H2,1-3H3,(H,10,12)
InChIKey
HFMAZNJKNNRONT-UHFFFAOYSA-N
SMILES
C(OC(C)(C)C)(=O)NC1(CO)CC1
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Safety

HS Code 
2924297099
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

TCI Chemical
Product number
B4251
Product name
[1-(tert-Butoxycarbonylamino)cyclopropyl]methanol
Purity
>97.0%(GC)
Packaging
200mg
Price
$37
Updated
2025/07/31
TCI Chemical
Product number
B4251
Product name
[1-(tert-Butoxycarbonylamino)cyclopropyl]methanol
Purity
>97.0%(GC)
Packaging
1g
Price
$119
Updated
2025/07/31
TRC
Product number
B809783
Product name
tert-ButylN-[1-(Hydroxymethyl)cyclopropyl]carbamate
Packaging
250mg
Price
$90
Updated
2021/12/16
Apolloscientific
Product number
OR350017
Product name
Boc-1-Aminocyclopropylmethanol
Purity
98%
Packaging
1g
Price
$37
Updated
2021/12/16
ChemScene
Product number
CS-D0180
Product name
tert-butyl(1-(hydroxymethyl)cyclopropyl)carbamate
Purity
>98.0%
Packaging
5g
Price
$78
Updated
2021/12/16
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tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate Chemical Properties,Usage,Production

Uses

Tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate could be converted into spirocyclopropanated analogues 14-CP and 14-CT of the insecticide Thiacloprid [1]. It can also be transformed into spirocyclopropanated analogs of Imidacloprid. This compound could be used to synthesize spirocyclopropanated five-membered ring analog 4-(3,5-Dichlorophenyl)-N-isopropyl-5-oxo-4,6-diazaspiro- [2.4]heptane-6-carboxamide[2].

Preparation

Tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate can be synthesized in three steps (40 % overall yield) from N, Ndibenzyl-2-benzyloxyacetamide starting with its reductive cyclopropanation (the de Meijere variant of the so-called Kulinkovich reaction). It can also be prepared in 56 % overall yield by monohydrolysis of commercially available diethyl cyclopropane-1,1-dicarboxylate followed by Curtius degradation of the carboxylic acid residue and subsequent reduction of the ester moiety[1].

Synthesis

107259-05-2

107017-73-2

General procedure for the synthesis of (1-hydroxymethylcyclopropyl)-tert-butoxycarbonylamino acids from ethyl 1-(BOC-amino)cyclopropanecarboxylate: ethyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate (4.31 g, 18.80 mmol) was dissolved in tetrahydrofuran (THF, 20 mL), and a 2M lithium borohydride (LiBH4) THF solution was slowly added dropwise ( 10.34 mL, 20.68 mmol), and the reaction mixture was stirred at room temperature overnight. Subsequently, a THF solution of 2M LiBH4 (5 mL, 10 mmol) was added additionally and stirring was continued at room temperature for 6 hours. Upon completion of the reaction, anhydrous sodium sulfate (Na2SO4, 15 g) and water (H2O, 10 mL) were added and the suspension was stirred at room temperature over the weekend. The suspension was filtered through a pad of sodium sulfate and the residue was washed with dichloromethane (DCM). The combined filtrates were concentrated under reduced pressure and the product was purified by column chromatography (silica gel, heptane/ethyl acetate, 1:1) to give 2.78 g of the target product in 79% yield.

References

[1] Brackmann F, et al. Synthesis of Spirocyclopropanated Analogues of Imidacloprid and Thiacloprid. European Journal of Organic Chemistry, 2005; 2005: 600-609.
[2] Brackmann F, et al. Synthesis of Spirocyclopropanated Analogues of Iprodione. European Journal of Organic Chemistry, 2005; 2005: 2250-2258.

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate Preparation Products And Raw materials

Raw materials

Preparation Products

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tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate Suppliers

Americas 1 China 193 Europe 1 India 4 Japan 1 Switzerland 1 United Kingdom 2 United States 13 Global 216
JW & Y Pharmlab Co., Ltd.
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021-64340559 13651849907;
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021- 64345308
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xinyu_shi@jwypharmlab.com.cn
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Tianjin Hexin Chengsai Science and Technology Development Co., Ltd.
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022-23410962 13752273685
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025-58851786 17714337195
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sales@tybiochem.com
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J & K SCIENTIFIC LTD.
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Chembest Research Laboratories Limited
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+86-21-20908456
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Sichuan Tongsheng Amino acids Co.,Ltd.
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0838-2274206 13908101207
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+86-838-2274207
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TCI (Shanghai) Development Co., Ltd.
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Sales-CN@TCIchemicals.com
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View Lastest Price from tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
Boc-1-Aminocyclopropylmethanol 107017-73-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-30
Career Henan Chemical Co
Product
N-BOC-1-AMINO-CYCLOPROPANEMETHANOL 107017-73-2
Price
US $5.50/KG
Min. Order
2KG
Purity
96%-99%
Supply Ability
100kg
Release date
2019-09-04

107017-73-2, tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamateRelated Search:

1-N-Boc-Aminocyclopentanecarboxylic acid Cyclopropyl carbinol 1-(Boc-amino)cyclopropanecarboxylic acid 1-AMINO-CYCLOPROPANEMETHANOL (1R,2S)-1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER 1-BOC-3-AMINOPIPERIDINE (1R,2R)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID Cyclopropanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-, (1R,2S)-rel- tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate 1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER (1R,2S)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID VINYL ACCA BOC-1-AMINO-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID (1S,2S)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID (1S,5R)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-1-CARBOXYLIC ACID 1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-,(1S,2R)- (1S,2R)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID (R)-BOC-1-AMINO-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID

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  • 107017-73-2