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

CAS NO.：107017-73-2
Empirical Formula: C9H17NO3
Molecular Weight: 187.24
MDL number: MFCD09749954
SAFETY DATA SHEET (SDS)
Update Date: 2024-04-24 17:21:40

What is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate?

The Uses of tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

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

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].

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.

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

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)

Safety information for tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P310:Immediately call a POISON CENTER or doctor/physician. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.