198404-98-7

Basic information

• Product Name: Cyclopropanemethanol,1-methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl]-
• Synonyms: Cyclopropanemethanol,1-methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl]-;(1-METHYL-2-(1,2,2-TRIMETHYLBICYCLO[3.1.0]HEX-3-YLMETHYL)CYCLOPROPYL)METHANOL
• CAS NO: 198404-98-7
• Molecular Formula: C15H26O
• Molecular Weight: 222.36634
• Mol File: 198404-98-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 270.4°C at 760 mmHg
• Flash Point: 120.9°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 0.000902mmHg at 25°C
• Refractive Index: 1.508
• PKA: 15.10±0.10(Predicted)
• Water Solubility: 3.8mg/L at 20℃
• CAS DataBase Reference: Cyclopropanemethanol,1-methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanemethanol,1-methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl]-(198404-98-7)
• EPA Substance Registry System: Cyclopropanemethanol,1-methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl]-(198404-98-7)

Safety Data

• Hazardous Substances Data: 198404-98-7(Hazardous Substances Data)

Usage

Chemical Properties

sandal cyclopropane is a colorless, viscous liquid with a powerful sandalwood odor with creamy and rosy undertones. It has a remarkably low odor threshold. The material is produced by a double Simmons–Smith cyclopropanation of 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol.

Flammability and Explosibility

Notclassified

Trade name

Javanol? (Givaudan)

InChI:InChI=1/C15H26O/c1-13(2)10(6-12-8-15(12,13)4)5-11-7-14(11,3)9-16/h10-12,16H,5-9H2,1-4H3

Upstream product

• 198405-38-8 (E)-(R)-2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-ol 
• 74-95-3 1,1-dibromomethane 
• 210115-64-3 (E)-2-methyl-4-((1S,3S,5R)-1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)but-2-en-1-ol 
• 1334212-53-1 C₁₉H₃₂O₂ 
• 1067637-16-4 (1-methyl-2-(((R)-2,2,3-trimethylcyclopent-3-en-1-yl)methyl)cyclopropyl)methanol 
• 1334212-54-2 (1R,3S,5S)-1,2,2-trimethyl-3-((2-methyl-2-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl)methyl)-6-oxabicyclo[3.1.0]hexane 
• 75-11-6 diiodomethane 
• 65114-01-4 (R)-2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal 
• 65114-01-4 (E)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-al 
• 1067637-16-4 (trans)-(1-methyl-2-(((R)-2,2,3-trimethylcyclopent-3-enyl)methyl)cyclopropyl)-methanol 
• 28219-60-5 Sandalmysore Core 
• 106155-02-6 2-methyl-4-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-but-2-en-1-ol 
• 74-97-5 chlorobromomethane 
• 23727-15-3 (+)-campholenic aldehyde 

Relevant articles and documents

Preparation method of dicyclopropane derivative compound

The invention provides a preparation method of a dicyclopropane derivative compound, and particularly relates to a preparation method of (1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hex-3-yl) methyl)cyclopropyl)methanol. The preparation method comprises the following steps: S1) mixing metal zinc, metal copper or salts thereof, halogenated acylate, acidic resin and a solvent, and carrying out an activation reaction to obtain an activated reaction solution; S2) alternately dropwise adding sandalwood 194 and dihalomethane into the activated reaction solution respectively, and after dropwise adding is completed, carrying out constant-temperature reaction on the system; S3) performing acidolysis on the system after the constant-temperature reaction, filtering to obtain an organic phase, combining the organic phase with liquid caustic soda, washing, and layering to obtain an organic phase containing a reaction product on the upper layer; and S4) carrying out rectification on the organic phase containing the reaction product to obtain (1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hex-3-yl) methyl)cyclopropyl)methanol.

CYCLOPROPANATION OF SUBSTITUTED ALKENES

Disclosed is a cyclopropanation process comprising the step of reacting an alkene compound having at least one carbon-carbon double bond with at least one dihaloalkane. The reaction is carried out in the presence of (i) particulate metal Zn, (ii) catalytically effective amount of particulate metal Cu or a salt thereof, (iii) at least one haloalkylsilane, and (iv) at least one solvent.

Transition-metal-catalyzed cyclopropanation of nonactivated alkenes in dibromomethane with triisobutylaluminum

The cyclopropanation of nonactivated alkenes with inexpensive triisobutylaluminum (TIBA), in dibromomethane as solvent and reagent, is efficiently catalyzed by FeCl3 at ambient temperature. Catalytic amounts of CuI salts, CpTiCl3, and [CpFe(CO) 2]2 are similarly effective. 2-Methylpropane, generated after quench of excess TIBA can be trapped, and excess dibromomethane can be recycled, which makes the method industrially applicable. Solvent-free DIBAH or TIBA reduction of unsaturated carbonyl compounds, followed by in situ TIBA cyclopropanation of the unsaturated aluminum alcoholates in dibromomethane give cyclopropyl alkanols. Dienols such as geraniol, linalool or nor-radjanol are selectively cyclopropanated in their distal position, which allows the synthesis of flavor and fragrance compounds such as δ-citral, cis-javanol, and 7-methyl-georgywood. Uncontrollable exothermic events are avoided due to relatively low reaction temperatures made possible by the catalysts and by the addition mode of the reagents.[1]